Phosphorus oxychloride → Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

HRID 2047710Notes

Reaction equation

HRID 2047710 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469588HCID 178469588, compound

Product 1

HCID 304558Ethyl 4-chloro-6-methoxyquinoline-3-carboxylateYield 97%

Procedure

A solution of ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate (Example 1c, 1.24 g, 5.0 mmol) in POCl3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale-yellow solid (1.29 g, 97%). 1H NMR (400 MHz, DMSO-d6) δ 1.36 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 7.57 (d, J=2.8 Hz, 1H), 7.61 (dd, J=2.8, 8.8 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was carefully quenched with ice
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with cold water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7029579ea313415b869da4257a9e356c
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

Loading…